#------------------------------------------------------------------------------ #$Date: 2025-09-04 16:03:39 +0100 (Thu, 04 Sep 2025) $ #$Revision: 302017 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/95/4519508.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4519508 loop_ _publ_author_name 'Abdel Rahman Al Ahmad' 'Thierry Maris' 'James D. Wuest' _publ_contact_author_id_orcid 0000-0001-9731-4046 _publ_section_title ; ArOCF3, ArOCHF2, ArOCH2F, and ArOCH3: What the F Does to Control the Crystallization of Riluzole and Analogous Fluoromethyl Ethers ; _journal_name_full 'Crystal growth & Design' _journal_page_first 6408 _journal_page_last 6420 _journal_paper_doi 10.1021/acs.cgd.5c00831 _journal_volume 25 _journal_year 2025 _chemical_formula_moiety '0.32(C8 H6 F2 N2 O S), 0.68(C8 H8 N2 O S)' _chemical_formula_sum 'C8 H7.37 F0.63 N2 O S' _chemical_formula_weight 191.60 _chemical_name_systematic ; 6-methoxy-1,3-benzothiazol-2-amine : 6-(difluoromethoxy)-1,3-benzothiazol-2-amine 0.68 : 0.32 ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_contact_author_email thierry.maris@umontreal.ca _audit_contact_author_name 'Thierry Maris' _audit_contact_author_phone '+1 514 340 4711 2579' _audit_creation_date 2024-12-06 _cell_angle_alpha 90 _cell_angle_beta 92.806(13) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 18.269(3) _cell_length_b 4.0563(7) _cell_length_c 11.5914(18) _cell_measurement_reflns_used 2145 _cell_measurement_temperature 150 _cell_measurement_theta_max 51.175 _cell_measurement_theta_min 4.217 _cell_volume 857.9(2) _computing_cell_refinement ; SAINT (2013) V8.41; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_collection ; APEX 4 (2022) Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_reduction ; SAINT (2013) V8.41; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 150 _diffrn_detector 'CMOS Area detector' _diffrn_detector_area_resol_mean 10.42 _diffrn_detector_type 'Bruker CMOS Photon III ' _diffrn_measured_fraction_theta_full 0.941 _diffrn_measured_fraction_theta_max 0.925 _diffrn_measurement_device 'k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker Venture Metaljet' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_collimation 'Focusing mirrors' _diffrn_radiation_monochromator 'Helios MX Mirror Optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Ga K\a' _diffrn_radiation_wavelength 1.34139 _diffrn_reflns_av_R_equivalents 0.0862 _diffrn_reflns_av_unetI/netI 0.0455 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 10330 _diffrn_reflns_point_group_measured_fraction_full 0.941 _diffrn_reflns_point_group_measured_fraction_max 0.925 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 55.248 _diffrn_reflns_theta_min 4.216 _diffrn_source 'Metal Jet' _diffrn_source_current 3.57 _diffrn_source_power 0.24897 _diffrn_source_target Ga _diffrn_source_type 'Gallium Liquid Metal Jet Source' _diffrn_source_voltage 69.74 _exptl_absorpt_coefficient_mu 2.038 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; TWINABS-2012/1 (Bruker,2012) was used for absorption correction. For component 1: wR2(int) was 0.1536 before and 0.0865 after correction. The Ratio of minimum to maximum transmission is 0.38. Final HKLF 4 output contains 14901 reflections, Rint = 0.0862 (4149 with I > 3sig(I), Rint = 0.0598) ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.483 _exptl_crystal_description platelet _exptl_crystal_F_000 396 _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.696 _refine_diff_density_min -0.390 _refine_diff_density_rms 0.079 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.611 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 129 _refine_ls_number_reflns 1510 _refine_ls_number_restraints 18 _refine_ls_restrained_S_all 1.617 _refine_ls_R_factor_all 0.1367 _refine_ls_R_factor_gt 0.1052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0821P)^2^+0.4139P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2596 _refine_ls_wR_factor_ref 0.2729 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 982 _reflns_number_total 1510 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 08-1b_1d_032RZ2F_068TZ_jw27293.cif _cod_data_source_block jw27293 _cod_database_code 4519508 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.13734(10) 0.8147(4) 0.28310(13) 0.0860(7) Uani 1 1 d . . . . . O1 O 0.4021(4) 0.462(2) 0.4300(8) 0.175(3) Uani 1 1 d . U . . . N1 N 0.0029(3) 0.7286(12) 0.3586(4) 0.0793(15) Uani 1 1 d . . . . . H1A H -0.029236 0.644409 0.404337 0.095 Uiso 1 1 calc R U . . . H1B H -0.012028 0.844829 0.297785 0.095 Uiso 1 1 calc R U . . . N2 N 0.1015(3) 0.5097(11) 0.4703(4) 0.0729(13) Uani 1 1 d . . . . . C1 C 0.0749(4) 0.6798(14) 0.3815(5) 0.0692(15) Uani 1 1 d . . . . . C2 C 0.2066(4) 0.6377(17) 0.3706(5) 0.0835(18) Uani 1 1 d . . . . . C3 C 0.1765(4) 0.4892(14) 0.4654(5) 0.0724(16) Uani 1 1 d . . . . . C4 C 0.2244(4) 0.3214(17) 0.5514(7) 0.091(2) Uani 1 1 d . . . . . H4 H 0.206109 0.214330 0.617009 0.110 Uiso 1 1 calc R U . . . C5 C 0.2960(5) 0.330(2) 0.5309(8) 0.109(2) Uani 1 1 d . . . . . H5 H 0.328715 0.225222 0.585565 0.131 Uiso 1 1 calc R U . . . C6 C 0.3267(4) 0.480(2) 0.4354(8) 0.109(2) Uani 1 1 d . . . . . C7 C 0.2822(4) 0.638(2) 0.3524(7) 0.102(2) Uani 1 1 d . . . . . H7 H 0.301657 0.741561 0.287011 0.123 Uiso 1 1 calc R U . . . C8 C 0.4369(6) 0.665(4) 0.3525(13) 0.169(4) Uani 1 1 d . U . A 1 H8A H 0.438259 0.554388 0.277499 0.254 Uiso 0.678(13) 1 calc R U P B 1 H8B H 0.486981 0.711010 0.382129 0.254 Uiso 0.678(13) 1 calc R U P B 1 H8C H 0.409744 0.872748 0.343379 0.254 Uiso 1 1 calc R U . A 1 F1 F 0.4222(10) 0.613(6) 0.238(2) 0.177(8) Uani 0.322(13) 1 d . U P B 2 F2 F 0.5063(9) 0.598(6) 0.3772(17) 0.168(7) Uani 0.322(13) 1 d . U P B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.1133(15) 0.0677(12) 0.0793(11) 0.0007(8) 0.0290(9) -0.0083(9) O1 0.105(5) 0.181(7) 0.242(8) 0.048(6) 0.048(5) 0.005(4) N1 0.105(4) 0.074(4) 0.058(3) 0.008(2) 0.009(3) -0.009(3) N2 0.097(4) 0.054(3) 0.068(3) -0.006(2) 0.012(2) -0.001(3) C1 0.095(4) 0.052(4) 0.061(3) -0.007(3) 0.005(3) 0.004(3) C2 0.097(5) 0.073(4) 0.082(4) -0.014(3) 0.022(3) -0.013(3) C3 0.092(4) 0.052(4) 0.074(3) -0.005(3) 0.011(3) -0.002(3) C4 0.082(4) 0.080(5) 0.113(5) -0.036(4) 0.018(4) -0.003(4) C5 0.111(6) 0.100(6) 0.117(6) 0.004(5) 0.009(5) 0.005(5) C6 0.082(5) 0.106(7) 0.142(7) 0.001(5) 0.019(5) 0.001(4) C7 0.101(6) 0.089(5) 0.118(5) 0.000(4) 0.025(5) -0.007(4) C8 0.100(6) 0.217(10) 0.195(9) 0.018(9) 0.048(7) -0.012(7) F1 0.104(10) 0.262(17) 0.167(14) -0.003(15) 0.032(11) 0.000(11) F2 0.091(10) 0.239(16) 0.175(12) 0.012(13) 0.002(9) -0.025(11) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0137 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.2925 0.4295 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 C2 S1 C1 88.3(3) . . C6 O1 C8 118.9(9) . . H1A N1 H1B 120.0 . . C1 N1 H1A 120.0 . . C1 N1 H1B 120.0 . . C1 N2 C3 109.3(5) . . N1 C1 S1 119.4(4) . . N2 C1 S1 116.7(5) . . N2 C1 N1 123.6(6) . . C3 C2 S1 109.6(5) . . C3 C2 C7 123.3(7) . . C7 C2 S1 127.1(6) . . N2 C3 C2 116.1(6) . . N2 C3 C4 124.3(6) . . C2 C3 C4 119.6(6) . . C3 C4 H4 122.5 . . C5 C4 C3 115.0(8) . . C5 C4 H4 122.5 . . C4 C5 H5 117.2 . . C4 C5 C6 125.6(8) . . C6 C5 H5 117.2 . . O1 C6 C5 116.8(8) . . O1 C6 C7 122.9(8) . . C7 C6 C5 120.3(7) . . C2 C7 H7 121.9 . . C6 C7 C2 116.2(7) . . C6 C7 H7 121.9 . . O1 C8 H8A 109.5 . . O1 C8 H8B 109.5 . . O1 C8 H8C 109.5 . . H8A C8 H8B 109.5 . . H8A C8 H8C 109.5 . . H8B C8 H8C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 S1 C1 1.740(6) . S1 C2 1.738(7) . O1 C6 1.384(9) . O1 C8 1.394(13) . N1 H1A 0.8800 . N1 H1B 0.8800 . N1 C1 1.343(8) . N2 C1 1.313(7) . N2 C3 1.376(7) . C2 C3 1.390(9) . C2 C7 1.407(9) . C3 C4 1.461(9) . C4 H4 0.9500 . C4 C5 1.342(10) . C5 H5 0.9500 . C5 C6 1.403(11) . C6 C7 1.387(11) . C7 H7 0.9500 . C8 H8A 0.9800 . C8 H8B 0.9800 . C8 H8C 0.9800 . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 S1 C2 C3 N2 0.4(7) . . . . S1 C2 C3 C4 179.7(4) . . . . S1 C2 C7 C6 179.8(6) . . . . O1 C6 C7 C2 -179.5(8) . . . . N2 C3 C4 C5 -179.9(6) . . . . C1 S1 C2 C3 0.7(4) . . . . C1 S1 C2 C7 -179.1(7) . . . . C1 N2 C3 C2 -1.6(7) . . . . C1 N2 C3 C4 179.1(5) . . . . C2 S1 C1 N1 -176.2(5) . . . . C2 S1 C1 N2 -1.8(5) . . . . C2 C3 C4 C5 0.8(9) . . . . C3 N2 C1 S1 2.2(6) . . . . C3 N2 C1 N1 176.4(5) . . . . C3 C2 C7 C6 0.0(11) . . . . C3 C4 C5 C6 -0.7(12) . . . . C4 C5 C6 O1 179.9(8) . . . . C4 C5 C6 C7 0.2(14) . . . . C5 C6 C7 C2 0.1(12) . . . . C7 C2 C3 N2 -179.8(6) . . . . C7 C2 C3 C4 -0.5(10) . . . . C8 O1 C6 C5 -166.1(10) . . . . C8 O1 C6 C7 13.6(16) . . . . _cod_database_fobs_code 4519508